(R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Base Information

• Chemical Name: (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate
• CAS No.: 158612-42-1
• Molecular Formula: C₂₂H₂₃N₃O₈
• Molecular Weight: 457.44
• Mol file: 158612-42-1.mol

Synonyms:(R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Chemical Property of (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

There total 5 articles about (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 66.0%

(R)-methyl pivaloyloxymethyl 2-formyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (158612-41-0) → (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (158612-42-1)

Guidance literature:

With hydroxylamine hydrochloride; sodium acetate; acetic anhydride; acetic acid;

DOI:10.1016/0957-4166(94)80108-8

Reference yield:

(S)-(+)-methyl pivaloyloxymethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (138279-12-6) → (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (158612-42-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / pyridinium bromoperbromide, pyridine / CH₂Cl₂ / 2 h / -20 °C

2: 27 percent / DMSO, NaHCO₃ / 2 h / 50 °C

3: 1.) NH₂OH*HCl, AcONa, AcOH, 2.) Ac₂O / 1.) RT, 1h, 2.) 100 deg C, 3 h

With pyridine; pyridinium perbromide hydrobromide; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; In dichloromethane;

DOI:10.1248/cpb.45.869

Reference yield:

bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (138279-16-0) → (R)-methyl pivaloyloxymethyl 2-cyano-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate (158612-42-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / H₂O / diisopropyl ether / 35 h / 25 °C / lipase AH from Pseudomonas sp.

2: acetone / 0 °C

3: collidine*HBr*Br₂, pyridine / CH₂Cl₂ / 5 h / -20 °C

4: 27 percent / DMSO, NaHCO₃

5: 66 percent / NH₂OH*HCl, Ac₂O, AcONa, AcOH

With pyridine; collidine*HBr*Br₂; hydroxylamine hydrochloride; water; sodium acetate; acetic anhydride; sodium hydrogencarbonate; acetic acid; dimethyl sulfoxide; In dichloromethane; di-isopropyl ether; acetone;

DOI:10.1016/0957-4166(94)80108-8

upstream raw materials:

(R)-methyl pivaloyloxymethyl 2-formyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

(S)-(+)-methyl pivaloyloxymethyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

(R)-methyl pivaloyloxymethyl 2-bromomethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

bis(pivaloyloxymethyl) 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate

Downstream raw materials:

(R)-2-cyano-1,4-dihydro-3-methoxycarbonyl-6-methyl-4-(3-nitrophenyl)-5-pyridinecarboxylate

(+)-Nilvadipine